(E)-N,N-dimethyl-2-(1-phenylprop-1-en-2-yl)-1H-indole-1-carboxamide | 1228117-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-N,N-dimethyl-2-(1-phenylprop-1-en-2-yl)-1H-indole-1-carboxamide
• 英文别名: N,N-dimethyl-2-[(E)-1-phenylprop-1-en-2-yl]indole-1-carboxamide
• CAS: 1228117-66-5
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: UQRNFIYLDQRXBS-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N,N-dimethyl-2-(1-phenylprop-1-en-2-yl)-1H-indole-1-carboxamide 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以85%的产率得到(E)-2-(1-phenylprop-1-en-2-yl)-1H-indole
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Intermolecular Hydroarylation of Alkynes

  摘要：

  The rhodium(III)-catalyzed hydroarylation of internal alkynes is described. Good yields are obtained for a variety of alkynes, and excellent regioselectivity is observed for unsymmetrically substituted alkynes. The reaction also gives good yields for a range of arenes. Preliminary mechanistic investigations suggest that this reaction proceeds through arene metalation with the cationic rhodium catalyst, which enables challenging intermolecular reactivity.

  DOI：

  10.1021/ja103080d
• 作为产物：
  描述：

  1-苯基-1-丙炔 、 N,N-dimethyl-1H-indole-1-carboxamide 在 tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate 、 三甲基乙酰氯 作用下， 以 醋酸异丙酯 为溶剂， 反应 16.0h， 以99%的产率得到(E)-N,N-dimethyl-2-(1-phenylprop-1-en-2-yl)-1H-indole-1-carboxamide
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Intermolecular Hydroarylation of Alkynes

  摘要：

  The rhodium(III)-catalyzed hydroarylation of internal alkynes is described. Good yields are obtained for a variety of alkynes, and excellent regioselectivity is observed for unsymmetrically substituted alkynes. The reaction also gives good yields for a range of arenes. Preliminary mechanistic investigations suggest that this reaction proceeds through arene metalation with the cationic rhodium catalyst, which enables challenging intermolecular reactivity.

  DOI：

  10.1021/ja103080d

文献信息

• Pyrroloindolone Synthesis via a Cp*Co^III-Catalyzed Redox-Neutral Directed C–H Alkenylation/Annulation Sequence
  作者：Hideya Ikemoto、Tatsuhiko Yoshino、Ken Sakata、Shigeki Matsunaga、Motomu Kanai

  DOI：10.1021/ja5008432

  日期：2014.4.9

  A unique synthetic utility of a Cp*Co(III) catalyst in comparison with related Cp*Rh(III) catalysts is described. A C2-selective indole alkenylation/annulation sequence proceeded smoothly with catalytic amount of a [Cp*Co(III)(C6H6)](PF6)2 complex and KOAc. Intramolecular addition of an alkenyl-Cp*Co species to a carbamoyl moiety gave pyrroloindolones in 58-89% yield in one pot. Clear difference was

  描述了 Cp*Co(III) 催化剂与相关 Cp*Rh(III) 催化剂相比的独特合成效用。C2 选择性吲哚烯基化/环化序列在催化量的 [Cp*Co(III)(C6H6)](PF6)2 复合物和 KOAc 的作用下顺利进行。将烯基-Cp*Co 物质分子内加成到氨基甲酰基部分，在一锅中以 58-89% 的产率得到吡咯并吲哚酮。在 Cp*Co(III) 配合物和 Cp*Rh(III) 配合物的催化活性之间观察到明显的差异，突出了有机钴物种独特的亲核活性。Cp*Co(III) 催化也适用于 N-氨基甲酰基吲哚的简单烯基化过程，广泛的炔烃，包括末端炔烃，适用于以 50-99% 的产率得到 C2-烯基化吲哚。
• Rhodium(III)-Catalyzed Intermolecular Hydroarylation of Alkynes
  作者：Derek J. Schipper、Marieke Hutchinson、Keith Fagnou

  DOI：10.1021/ja103080d

  日期：2010.5.26

  The rhodium(III)-catalyzed hydroarylation of internal alkynes is described. Good yields are obtained for a variety of alkynes, and excellent regioselectivity is observed for unsymmetrically substituted alkynes. The reaction also gives good yields for a range of arenes. Preliminary mechanistic investigations suggest that this reaction proceeds through arene metalation with the cationic rhodium catalyst, which enables challenging intermolecular reactivity.